Cannabis sativa cannabinoids from

TauraF, Morimoto S, Shoyama Y, Cannabis. 23. CannabineroHc acid, a cannabinoid from Cannabis sativa, Phytochemistry 39, 457- 58, 1995. 

Appendino G, Giana A, Gibbons S, Maffei M, Gnavi G, Grassi G, Sterner OA (2008) A polar Cannabinoid from Cannabis sativa var. Carma. Nat Prod Conunun 3 1977... 

Han us L, Krejci Z, Isolation of two new cannabinoid acids from Cannabis sativa L, of Czechoslovak origin, Acta Univ Olomuc Fac Med 74 161-166, 1975. 

CS145 llanus, L. and K. Tesarik. Capillary gas CS156 chromatography of natural substances from Cannabis sativa L. III. Content of cannabinoids in dried roots. Acta Univ Palacki Olomuc Fac Med 1987 CS157... 

Delta-9-THC is the main active constituent extracted from Cannabis sativa (Tuner, 1985 in Marijuana 1984, Ed. Harvey, DY, IRL Press, Oxford). Numerous articles have described not only psychotropic effects of cannabinoids but also their influence on the immune function [Hollister L. E., J. Psychoact. Drugs 24 (1992) 159-164]. The majority of in vitro studies have shown that cannabinoids have immunosuppressant effects inhibition of the mitogen induced proliferative responses of T lymphocytes and B lymphocytes [Luo, Y. D. et ah, Int. J. Immuno-pharmacol. (1992) 14,49-56 Schwartz, H. et at., J. Neuroimmunol. (1994) 55,107-115], inhibition of the activity of cytotoxic T cells [Klein et at., J. Toxicol. Environ. Health (1991) 32, 465-477], inhibition of the microbicidal activity of macrophages and of TNF-a synthesis [Arata, S. et at.. Life Sci. (1991) 49, 473-479 Fisher-Stenger et al., J. Pharm. Exp. Then (1993) 267, 1558-1565] and inhibition of the cytolytic activity and the TNFa production of large granular lymphoc3rtes [Kusher et al.. Cell. Immun. (1994) 154, 99-108],... 

A >tetrahydrocannabinol is one of the active principles of cannabis (constituent of marijuana or hashish from Cannabis sativa) with lower psychoactivity than A -tetrahydrocannabinol. It is a cannabinoid receptor agonist and has (euphoric) sedative and mild PSYCHOTROPIC (hallucinogenic) properties, and ANTIEMETIC activity. A >tetrahydrocannabinol (A -tetrahydrocannabinol) is an active cannabinoid. It is a constituent of marijuana. The active (6aR,10aR)-(-)-trans-form = dronabinol. It is a CANNABINOID RECEPTOR AGONIST and has (euphoric) SEDATIVE and mild PSYCHOTROPIC (hallucinogenic) properties, and ANTIEMETIC activity. 

Epi-gallocatechine-3-gallate (EGCG) Cannabinoids (cannabidiol from Cannabis sativa) Capsaicin Carotenoids P-Carotene... 

A myriad of natural compounds have been tested for the past 20 years in a frenetic search for agents with potential effects against AD neuropathology. Some of these compounds include alkaloids from the calabar bean (Physostigma venenosum) huperzine A from Huperzia serrata-, galantamine from the snowdrop Galanthus woronowii cannabinoids (cannabidiol from Cannabis sativa) ... 

Cannabinoids.—New compounds (259 OH at C-8 or at C-10)847 and (259 OH at both C-9 and C-10)848 have been isolated from Cannabis sativa. p-Menth-2-ene-1,8-diol is an excellent synthon for the A9-tetrahydrocannabinol (THC) skeleton, coupling (ZnCl2-catalysed) with olivetol (3-n-pentylresorcinol) to form the (—)-parent compound, and forming the biologically potent 3-OH metabolite by appropriate modification of the reaction.849 The structurally equivalent substrate p-menth-1,8-dien-1 -ol reacted with other substituted resorcinols and led to A8- and A9-THC analogues differing in the side-chain attached at C-3.850-851 Use of the synthon (260) in a similar manner gave 2, 1 l-dihydroxy-A9-THC this was claimed... 

Of potential interest and relevance to cannabinoid analgesia is the recent observation that some novel prenylflavonoids isolated from Cannabis sativa exhibit anti-inflammatory activity [145b],... 

A water-soluble non-cannabinoid fraction from Cannabis sativa has been found to reduce IOP [216-219]. It is apparently a glycoprotein. It seems strange that a plant should contain both small molecules (cannabinoids) and biopolymers with the same kind of activity. 

Tetrahydrocannabivarinic acid, cannabidivarinic acid, cannabichromevarinic acid, and cannabigerovarinic acid are the C-3" carboxylic acid derivatives of known propyl side-chain cannabinoids, ° and others are propyl homologues of cannabichromanone, cannabielsoin, and cannabielsoic acid Turner et al. have reported an additional triol (240) from Cannabis sativa ... 

Cannabinoids are natural bi- and tricyclic products (approximately 60) isolated from Cannabis sativa which have a structure related to A9-tetrahydrocannabinol (THC). 

Cannabinoids Chemicals synthesised from precursor terpenes in Cannabis sativa including cannabidiol, cannibinol and THC. 

In their next study, Shoyama and Nishioka isolated new spirocom-pounds cannabispirol and acetyl cannabispirol. This is in addition to the already known cannabispirone and cannabispirenone from a Japanese hemp variety. The two scientists included them in their biogenetic schema alongside the cannabinoid acids. In a further study, Shoyama et al. dealt with the biosynthesis of propylcannabinoid acids by in vitro incubation with raw enzyme solution from three species of Cannabis sativa KL. A biogenetic schema is presented illustrating the relationship between methyl, propyl and pentyl cannabinoid acids. 

Ross SA, ElSohly MA, Sultana CNN, Mehmedic Z, Hossain CF, Chandra S, Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L, PhytochemAnal 16 45—48, 2005. 

Cannabinoids are isolated from the plant Cannabis sativa,... 

Cannabinoids are the psychoactive components of marijuana, which has the species name Cannabis sativa. Concentrations of cannabinoids vary greatly from plant to plant. The original strains of this plant species contain very little of these psychoactive components and have been used for many centuries for their great fiber qualities. Strains of Cannabis that may be smoked for psychoactive effects on average contain about 4 percent cannabinoid derivatives. The most active of these derivatives is the compound A9-tetrahydrocannabinol (THC), shown in Figure 14.33 on page 504. 

The resin secreted by Cannabis indica and Cannabis sativa, varieties of hemp, is known variously as marijuana, hashish or bhang and is abused as a hallucinogenic drug. It appears however to have some beneficial properties and is currently under test as an antiemetic in cancer therapy. The secretion contains a number of interrelated oxygen heterocycles, some of which are shown in Scheme 281, which attempts to indicate their biosynthetic relationships (70MI22401). The cannabinoids are probably derived from a monoterpene unit based on p-menthane and 5-n-pentylresorcinol (olivetol), acting the part of a polyketide. 2,2-Dimethylchromene biosynthesis also requires the intervention of an isoprene fragment. 

Hexanoate is also likely to feature as a starter unit in the formation of the cannabinoids, a group of terpenophenolics found in Indian hemp (Cannabis sativa Cannabaceae). This plant, and preparations from it, known under a variety of names including hashish, marihuana, pot, bhang, charas, and dagga, have been used for centuries for the pleasurable sensations and mild euphoria experienced after its consumption, usually by smoking. 

The history of the use and identification of Cannabis sativa L. is long and complex. It is one of the oldest cultivated plants, used for the production of oil from the seeds, and fibre from the stems for rope and fabrics, and has long been used as a psychoactive drug due to the presence of cannabinoids in the resins produced by the plant. Indeed, there is evidence of cannabis use from Neolithic burial sites. The name Cannabis sativa was first used in Linnaeus Genera Plantarum in 1753, but since that publication there has been considerable debate about the number of species and varieties that exist - this has been recently summarized succinctly by Gigliano [1]. The debate has centred on (i) the characteristics of the fruit, and (ii) meiosis and pollen fertility. It is now generally accepted, however, that there is only one species, namely Cannabis sativa L., which exhibits great diversity due to both selection in the wild and in the cultivated environment. 

Cannabinoids are a group of C2i compounds found in the plant species Cannabis sativa. The principal psychoactive cannabinoid is A -tetrahydrocannabinol (THC) (Figure 34-29). THC is typically consumed by smoking marijuana, which is a mixture of crushed leaves, flowers, and sometimes stems from the cannabis plant. Hashish, the dried, resinous... 

Marijuana, or Cannabis sativa, has been valued for its medicinal as well as its psychotropic properties dating back to ancient times. However, reports from as early as the 1960s have indicated that marijuana and select components also could compromise human health, including the ability to resist infections. Included among these components is a class of compounds collectively known as cannabinoids. At least 60 have been identified. These include cannabidiol (CBD), cannabinol (CBN), cannabigerol (CBG), and A -tetrahydrocannabinol (THC), the major psychoactive ingredient in marijuana that has been implicated as the major immunomodulatory substance. 

Cannabinoids, the active components of Cannabis sativa and their derivatives, act in organisms by mimicking endogenous substances—the endocannabinoids anandamide and 2-arachidonoylglycerol—that bind to and activate specific cannabinoid receptors. So far, two cannabinoid-specific Gj/o protein-coupled receptors, CBl (Matsuda et al. 1990) and CB2 (Munro et al. 1993), have been cloned and characterised from mammalian tissues. Most of the effects of cannabinoids rely on CBi receptor activation. This receptor is particularly abundant in discrete areas of the brain, but is also expressed in peripheral nerve terminals and various extra-neural sites such as testis, eye, vascular endothelium and spleen. In contrast, the CB2 receptor is almost exclusively present in the immune system (Howlett et al. 2002). 

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